2,4,6-Trimethylpyridine → HCID 11361091, compound

HRID 2216302Notes

Reaction equation

HRID 2216302 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[C:13]([NH:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])=[N:14][C:15]([CH3:18])=[N:16][CH:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Li+].[I-].N1C(C)=CC(C)=CC=1C>CCOCC>[CH3:18][C:15]1[N:14]=[C:13]([NH:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[C:12]([S:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)(=[O:11])=[O:10])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 66321Lithium iodideHCID 11452287HCID 11452287, compound

Product 1

HCID 11361091HCID 11361091, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of [5-(4-methoxy-benzenesulfonyl)-2-methyl-pyrimidin-4-yl]-(2,4,6-trimethylphenyl)-amine (300 mg, 0.75 mmol), prepared as described in Example 1, LiI (2.0 g, 15 mmol) and 2,4,6-collidine (5 mL) was refluxed under N2 for 2 h and then cooled to room temperature. The reaction mixture was diluted with Et2O, and extracted (4×) with 2 N NaOH. The combined aqueous layers were washed with ether, neutralized with 3 N HCl to pH=7.0 and then were extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (50:50 hexanes/EtOAc) to provide the desired product (271 mg, 93%) as a white solid: mp 246–248° C.; 1H NMR (300 MHz, CDCl3) δ 8.69 (s, 1H), 8.30 (br s, 1H), 7.82 (d, J=8.7 Hz, 2H), 6.92 (s, 2H), 6.89 (d, J=8.7 Hz, 2H), 2.40 (s, 3H), 2.31 (s, 3H), 2.03 (s, 6H); APCI MS m/z 384 [(M+H)+, calcd for C20H22N3O3S, 384.1].

Workup

  1. customprepared
  2. temperaturewas refluxed under N2 for 2 h
  3. extractionextracted (4×) with 2 N NaOH
  4. washThe combined aqueous layers were washed with ether
  5. extractionwere extracted three times with CH2Cl2
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by chromatography on silica gel (50:50 hexanes/EtOAc)

Sources & evidence

ORD record
ord-85bce3caf032446aaaa4a5b07432a516
Source dataset
uspto-grants-2006_09
Patent number
US07112585B2

Reaction notes

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